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Water → 4-Hydroxymethylbicyclo[2.2.2]octane-1-carboxylic acid benzyl ester

HRID 480169
Notes
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Reaction equation

HRID 480169 reaction equation
[CH3:1][O:2][C:3]([C:5]12[CH2:12][CH2:11][C:8]([C:13]3NC4C(=O)N(CCC)C(=O)N(CCC)C=4N=3)([CH2:9][CH2:10]1)[CH2:7][CH2:6]2)=[O:4].C(=O)([O-])[O-].[K+].[K+].C(Br)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[OH2:44]>CN(C=O)C.C(OCC)(=O)C.CCCCCC>[CH2:1]([O:2][C:3]([C:5]12[CH2:6][CH2:7][C:8]([CH2:13][OH:44])([CH2:9][CH2:10]1)[CH2:11][CH2:12]2)=[O:4])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 98440604-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester

Product 1

HCID 865917484-Hydroxymethylbicyclo[2.2.2]octane-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 21226206Ethyl acetate hexaneSolvent

Procedure

4-Hydroxymethylbicyclo[2.2.2]octane-1-carboxylic acid (XVII, Example 14, 24.8 g 135 mmol) is dissolved in DMF (950 ml). Anhydrous potassium carbonate (25 g, 181 mmol) is added to the solution slowly. Benzyl bromide (22 g, 12.94 mmol) is then added. The reaction mixture is heated at 80° for 16 hr. To the reaction mixture is added water (150 ml) and concentrated to give an oil, which was dissolved in ethyl acetate/hexane (5/1, 500 ml). The mixture is washed with saline (2×200 ml), dried over anhydrous sodium sulfate and concentrated to give the title compound, NMR (400 MHz, CDCl3) δ 7.39, 5.11, 3.28, 1.84 and 1.41.

Workup

  1. temperatureThe reaction mixture is heated at 80° for 16 hr
  2. concentrationconcentrated
  3. customto give an oil, which
  4. washThe mixture is washed with saline (2×200 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f8df21a4be864beb8a131d903dcf9064
Source dataset
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06649600B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes